General procedure for the synthesis of 6-methoxy-2-pyridinemethanol from 6-methoxypyridine-2-carboxylic acid methyl ester: 6-methoxypyridine-2-carboxylic acid methyl ester (2 g, 11.96 mmol) was dissolved in anhydrous methanol (20 mL) and cooled down to 0 °C under nitrogen protection. Sodium borohydride (1.36 g, 35.89 mmol) was slowly added and the reaction system was kept stirred at 0 °C for 30 min. Subsequently, the reaction system was slowly warmed to room temperature and stirring was continued for 1 hour. After completion of the reaction, the reaction was quenched with water and the reaction mixture was concentrated on a rotary evaporator. The concentrated mixture was diluted with brine (100 mL) and then extracted with a mixture of dichloromethane and 2-propanol (2:1, 3 x 150 mL, by volume). The organic phases were combined, dried with magnesium sulfate, filtered, and concentrated on a rotary evaporator to give 6-methoxy-2-pyridinemethanol (500 mg, 30% yield) as an oily product. Mass spectrometry analysis showed [M+H]+ calculated value of 140.1 and measured value of 140.1.
